Ammonia → HCID 22484549、化合物

HRID 2180962

反応式

HRID 2180962 の反応式
N.[Na].C([N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:13]=2[CH:12]=[CH:11]1)C1C=CC=CC=1>CCOCC>[CH:20]1([O:19][C:18]2[C:13]3[CH:12]=[CH:11][NH:10][C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 5360545SodiumHCID 224845557-Benzyl-4-cyclohexyloxy-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 22484549HCID 22484549、化合物収率 9.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To liquid ammonia (6.0 mL) at −78° C. was added 33 mg (1.43 mmol) sodium metal and the resulting dark blue solution stirred at −78° C. 10 min. A solution of 75 mg (0.244 mmol) of the product from Method M in 3.0 mL of ether was added dropwise over a 5 min period. The resulting solution stirred at −78° C. for 1 h followed by quenching upon addition of 500 mg of solid ammonium chloride. After evaporation at room temperature, the residual solid was triturated with 25 mL of ethylacetate containing 1 mL of acetic acid for 1 h. Filtration and concetration in vacuo afforded crude material which was purified by preparative thin layer chromatography (silica-gel; 2:1 ethyl acetate/hexanes) to produce 5 mg of the title compound. 1H NMR (400 MHz) (CDCl3) δ: 1.27-1.35 (m, 6H), 1.62-1.67 (m, 4H), 5.30-5.36 (m, 1H), 6.55 (d, 1H, J=3.2 Hz), 7.11 (d, 1H, J=3.2 Hz), 8.37 (br s, 1H). LRMS: 218.2 (M+1).

後処理

  1. custom10 min
  2. stirringThe resulting solution stirred at −78° C. for 1 h
  3. customby quenching upon addition of 500 mg of solid ammonium chloride
  4. customAfter evaporation at room temperature
  5. customthe residual solid was triturated with 25 mL of ethylacetate containing 1 mL of acetic acid for 1 h
  6. filtrationFiltration and concetration in vacuo
  7. customafforded crude material which
  8. customwas purified by preparative thin layer chromatography (silica-gel; 2:1 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-04c9eecfe31144cdab513d479ad4f92f
出典データセット
uspto-grants-2005_05
特許番号
US06890929B2

関連ノート

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